Synthetic Studies Towards Milbemycin β3. Rapid Construction of a Model Spiroketal Subunit Using the Intramolecular Silyl Modified Sakurai (ISMS) Methodology

István E. Markó; Mark Bailey; Fiona Murphy; Jean-Paul Declercq; Bernard Tinant; Jeanine Feneau-Dupont; Alan Krief; Willy Dumont

doi:10.1055/s-1995-4858

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Synlett 1995; 1995(1): 123-126
DOI: 10.1055/s-1995-4858

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Synthetic Studies Towards Milbemycin β₃. Rapid Construction of a Model Spiroketal Subunit Using the Intramolecular Silyl Modified Sakurai (ISMS) Methodology

István E. Markó¹ , Mark Bailey¹ , Fiona Murphy¹ , Jean-Paul Declercq¹ , Bernard Tinant¹ , Jeanine Feneau-Dupont¹ , Alan Krief² , Willy Dumont²

¹Département de Chimie, Université Catholique de Louvain, Place Louis Pasteur 1, B1348 Louvain-La-Neuve, Belgium
²Laboratoire de Chimie Organique, Facultés Notre-Dame de la Paix, 3000 Namur, Belgium

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Publikationsdatum:
31. Dezember 2000 (online)

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The ISMS condensation between allyl silane 3 and ortholactone 13 smoothly leads, after oxidative cleavage and stereoselective reduction, to spiroketal 2b, a model for the subunit present in milbemycin β₃.

Milbemycin - spiroketal - ISMS condensation - allyl silane - oxonium